Some days you feel sexier than others. Fridays are usually my day for feeling sexy. Maybe it’s because it’s the end of the work week or maybe it’s because that’s traditionally the day to take back our energy from whatever it is we do for a living. Yesterday was Friday.

In a perfect world I would be able to wear a cute outfit as I go to work and finish my week with a smile; however, it’s not a perfect world, so I put my stockings, panties, and short tight little black dress on under my normal uniform. ‘Underdressing’ is what it’s called.

My normal work uniform consists of a t-shirt, a button up maintenance shirt, and black jeans. Yes, I am in maintenance and therefore no cute shoes either. Boots, and since boots and stockings just don’t work I put on white sweat socks on top of the cute black stockings and then my boots. Taking a look in the full-length mirror in my bedroom I smiled and felt pretty. Little did I know what would happen in a few hours.

Crossdresser Heaven - Find Your Tribe

Fridays are busy and heavy for me at work. They always have been and always will be and I had a lot of layers on. Before the first two hours of work had finished I was sweating through my pretty black dress, t-shirt, and uniform shirt. I had to take the dress off or make a terrible showing of myself. Now comes the problem of where to put it. It’s little but it won’t fit in my pocket and if I just carry it out of the bathroom and put it in a cupboard then everyone will see and ask what it is? What am I going to do?

Sadly, I had to toss the dress. I wrapped it in some paper towels and put it on the bottom of the basket. I started my day feeling cute and sexy and ended without a dress and feeling drab.

But something happened that was more important than the loss of a dress. I, of course, initially went to that dark place we all know. Feeling alone and ashamed I continued doing my job under this cloud. We all know this place. It’s an internal landscape of judgment and shame. “Why am I so damn weird?” and “Why can’t I just be a normal man?” echoed in my own voice through my head. A person can feel so lonesome with these voices your only companion.

That’s when I remembered Crossdresser Heaven. Crossdresser Heaven is filled with people just like me. Everyone here has similar feelings, the same questions bounce around their heads, and most here have traveled the same path that I am and that made me feel better. The dark cloud lifted and I accepted myself a little bit more. I, like everyone here, am perfectly me. Whether in pants and boots or in a slip, dress, and makeup, we should continue to rejoice in the beauty and diversity of ourselves. Like a stained glass window that the sun is shining through we are a picture of mixed up beautiful colored landscape.

Never stop being yourselves, ladies and gentlemen. We are just as important and needed as everyone else.

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Jessica

Jessica McKnight is a new cross dresser who has discovered her gender-fluidity in her late forties. With painted toes, and a lipstick smile she attempts to shine her way into a new and accepting life as Jessica.

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39 Comments
  1. Amanda fine Wheeler 3 weeks ago

    I’m Amanda and I have been crossdressing since I can remember. I have also been suffering from deppresion because I have to hide my true self. I love wearing pantyhose and heels dresses and panties, but I’ve know for about 4 years that I’m bout sexual and love feeling girlie my gf knew about it and wen we split up 3 weeks ago she outed me I denied it but am so ashamed I wish I had the nerve to come out . Am I a coward? No . I’m a beautiful woman inside, wow I’m so confused

    • Author
      Jessica 2 weeks ago

      Amanda-
      No you aren’t a coward, and she shouldn’t have outed you. You are a beautiful person inside and that isn’t confusing. You are who you are and there isn’t any shame in it.
      Thanks for sharing and good luck with things.
      Jess

  2. tina Smith 3 weeks ago

    Great article. It is a war sometimes as we try suppress what wants to come out. I have accepted the feminine me so it’s not so bad now. But she wants to spend money like it grows on trees lol. I now have just about as much women’s wear as my other half. It’s hard to keep her in check when she see’s a beautiful dress or skirt or a new pair of heels. Or the latest in make-up lol. More often than not she wins which is ok.

  3. Lisa 3 weeks ago

    It is so good to know I am not alone. I do not pass as a women. I also wear feminine clothing under my boring men’s clothes.

    I do not like rejection so women’s shorts, panties, bra, and small tank top is about as far as I dare go.

    I am still learning to accept myself and love me as I am.

  4. Ashleigh 4 weeks ago

    Thanks for sharing this. I understand, as do most of us here, about wanting just to be able to dress the ay we want to. Underdressing is definitely a great outlet for expression of our feminine persona. I have become more bold over recent years and have started wearing mostly female clothing all the time. You’d be surprised what you can “get away with” if you choose carefully. Jeans, sneakers, and other garments can look fairly generic, yet make all the difference in the world in how we feel.

    • Author
      Jessica 4 weeks ago

      Ashleigh-
      Good for you. I have begun to do that as well.

  5. Stef Smith 4 weeks ago

    Oh for the day when we all can just be.
    I d love to wear a pair of high waist skinny jeans strappy heels and a nice top with all the underthings
    And just go out for a normal day
    But not yet!

    • Author
      Jessica 4 weeks ago

      Stef-
      I know what you mean. I want to wear a knee high skirt, flats, and any old shirt out and just be a regular day.

  6. Karyn 4 weeks ago

    Hi Jessica,
    Thank you for the nice post to read. I, like the rest of the girls, wish with all my heart I had been born female. You and I definately have the same thoughts on the locker room talk. It is inappropriate and disrespectful. It seems I am in that dark place you mentioned. I too feel ashamed and wish I was like other men out there, but I love being girlie, and feel 100% the way I feel inside. I have been this way for as long as I can remember. I came out to my wife two years ago, and she says she is supportive. I do under dress, and wear panties, a cami, knee high stockings, earrings, and pretty smelling perfume and lotion. I have also come out to my sister, a male friend, and several female friends who are very supportive. I can share my feelings with them, but not like I can with another transgender friends. My wife and I don’t talk too much about it though. I wish we did very much. Thank you so much for sharing your thoughts and experiences. I need to read these stories on occasion to confirm, and reinforce, there are a lot of people like us out there. Hugs

    • Author
      Jessica 4 weeks ago

      Karyn-
      It’s great to know there are other girls like us around. It took a while for my wife and I to chat more about it but now we can easily chat.

  7. janedon 4 weeks ago

    Quite the subject- I see the unpleasantness & complications boiling down to two basic problems—Religion/control & Money /Control–

    • Author
      Jessica 4 weeks ago

      Janedon-
      Everything seems to come back to control doesn’t it.

  8. Terri 1 month ago

    Thank you Jessica for sharing your story. Even after all these years of going out as Terri, it still feels good to know that I am not alone in my struggle.

    • Author
      Jessica 4 weeks ago

      Terri-
      I’m very glad that we aren’t alone in this.

  9. Trisha Anne 1 month ago

    Thank you for sharing Jessica! As a partner, not a CD, articles like yours help me better understand the struggle my love deals with every day. It’s heart breaking to hear the questions you ask yourself, like “why am I so damn weird?” because I hate to think she has those same thoughts. I too am grateful for CDH, maybe for different reasons, and for members like you who share pieces of yourself that add to my understanding and help me love my sweetheart better.

    • Author
      Jessica 1 month ago

      Trisha-
      Thank you for telling me this. All of the response has really been amazing. I think that the answer to the question of being weird is either that a person isn’t or if they are there are a whole bucket full of other folks who are just as wonderfully weird and gorgerous and that’s beautiful.
      Thanks again for your response.
      Jess

  10. Faye Lambert 1 month ago

    This is an awesome read! Yes, we’ traveling the same path. I can definitely relate to the feeling of shame. My “Christian” upbringing makes me feel ashamed of who I am. I am beginning to embrace who I am. I didn’t pick this journey. I was one of the chosen to take this journey. I will continue to walk with my head held high.

    • Author
      Jessica 1 month ago

      Faye
      “These boots are made for walking.”
      Keep on walking girl.
      Jess

  11. Alexis Frazier 1 month ago

    Jessica, Thank you for this article that is so personal. I am dreaming of some days I can underdress regularly like you. Seems like you struck a nerve that resonated with several members. Thanks for being the encourager that I needed.

    Alexis

    • Author
      Jessica 1 month ago

      Alexis-

      It was just meant as a thank you to all of the ladies here. I am grateful.
      Jess

  12. Marianne 1 month ago

    Jessica, thank you for your willingness to share youre ups and downs with us here on CDH. As for myself I have very seldom asked why. I accepted being girl in mind very young and always wished I had gotten a body to match that. Still it took 35 years of secret dressing before I could fulfill my longtime whish to go out dressed as a woman and yet a couple of years before i started coming out to friends and family

    • Author
      Jessica 1 month ago

      Marianne-
      I have read so many heartfelt things here from ladies just like me. I’m glad to hear that you can be yourself now. (If I read your letter right) I have just recently figured out what all of that was about, and so it’s all very exciting for me.
      Hugs
      Jess

  13. skippy1965(Cynthia) 1 month ago

    Love the story Jessica. While i’m not as open as I want to be about Cyn, I am comfortable in my stealth dressing where all my clothes are actually women’s clothes even if no obviously so. And while I used to-and on rare occasions still-wish that I was not “different” than guys, I have come to accept and love all of who I am and realize Cyn is a large-and perhaps the MOST part of what makes me who I am and that’s a GOOD thing!
    Cyn

    • Author
      Jessica 1 month ago

      Cyn

      I have been slowly switching my clothing so I have and wear more women so clothes. While it’s not all the time it is a lot. Almost always in panties shoes, and a bra (the sports variety can’t really be noticed under-dressed).
      Thanks for reading.
      Jess

  14. Rachel Ní D 1 month ago

    Hi Jessica.

    I loved your article, like others I’ve had similar feelings to you and why is still a constant question in my mind. Whilst I’ve never thought of myself as “odd” or “weird”, I’ve lost count of the times I wish I’d been born fully female, or wondered how much more straightforward life would be I was a normal man. I absolutely *despise* having to wear the suit/shirt/tie combination , it might be in my head of course, but I’ve yet to find a suit that even feels comfortable on (even if it’s a good fit). Fortunately I work in IT, so can get away with the usual jeans, t-shirt and proverbial combat boots on a day to day basis, but even that might be on borrowed time as the company has a new owner with a much more formal dress code. Whilst nothing has been said to me, yet, I’m dreading having to conform to that.

    There’s many days I’m happy to not be the “normal man” too though. I see plenty of them around and there’s little I admire with the pointless locker room talk, aggressiveness and general bravado. I’ve a good few very close female friends that I can chat with in a way I doubt I could if I was “normal man” , and I absolutely treasure the friendship with them. I’ve not told them about Rachel, but I wonder if they can pick up on her somehow.

    It can be a very lonely path sometimes, I’m also glad to have found this place and know that it’s not just me on this journey.

    Rachel.
    xxx

    • Author
      Jessica 1 month ago

      Rachel-
      Thanks for reading my article! I’ve never understood the ‘locker room’ talk either. It’s just another way to feel superior.
      Hugs Jess

  15. Gisela Claudine 1 month ago

    I appreciate your moving article, Jessica.
    I am a hider, coming back and forth. In a way I enjoy what some would call my dance between genders, although sometimes it is complicated. Well. Life ain’t easy. Occassionally I suffer the pressure of the society in which I live. I would like not to have to worry about others value my way of life and I restrict myself so as not to cause unnecessary suffering to my loved ones, but I have to value myself and look for a balance. I do not fight against myself anymore. Well. Most of the time. I chase away my fears and my demons.
    It hurts when I don’t find time to enjoy it even in a simple way. Sometimes I just need perfume, panties, bra, shorts and a blouse to enjoy feminity. It is mostly in my mind and soul, I guess. I call it crossdressing my soul. I am still learning to understand the transgender woman in me. I love her. I love myself. It is the only way to be able to love others. Fortunately, I count on Crossdresser Heaven and my supportive sisters. I enjoy that space to be me.

    • Author
      Jessica 1 month ago

      Gisela-
      I have to admit that as I’ve gotten older I care less and less for other people’s opinions on what I do or who I am. It has been so freeing. I sort of like to think of it as a gift.

  16. Khloe West 1 month ago

    Well stated and appreciated!

    I’m rather a lucky duck, in that I get to “dress” a little on the daily. Denim and a top a ubiquitous look, but all of ine are from that “Other side of the aisle”,

    Self employed for 3+ decades as a handyman with private clients. It ~was~ a bit of an adjustment to myself and the client base when I first discovered the real me in my early 50’s and started the changes.

    *Footnote* I was innocently, yet utterly unexpectedly, “outed” on my first “girl’s night out” and simply rolled with it and owned that side of me in daily life. It’s certainly had it’s moments, but ultimately a great decision to go that route. *End Footnote*

    Lady outer wear almost 24/7 (I save the ill fitting “boy duds” for crawling about in attics and under houses), even if only “lady” jeans and T’s. Painted nails top and bottom on the 24/7 as well.

    It’s been a bit of an adjustment phase, but it’s all running well.

    • Author
      Jessica 1 month ago

      Not till your 50’s? Well, I’m almost 50 myself actually. I’m glad you’re able to dress and be comfy in your own skin. That’s great. I’m rather excited about where this is going.
      Thank you for sharing.
      Jess

  17. Miss P 1 month ago

    Jessica, Thank you for not only sharing the pain of having to hide away the little black dress but also part of who you are. As you, I have my own experiences of hiding away and losing not only items but self esteem. The wondering of “Why am I like this,” has been a refrain echoing in my brain. I am glad for your sharing which strengthens me and helps me connect with you, with others, and myself. I appreciate your gift.

    • Author
      Jessica 1 month ago

      Miss P.
      Thank you for the comment. You know I have way more self esteem now that I’ve discovered and connected with so many other folks just like me. It’s turned into a lovely journey.

      • Miss P 1 month ago

        That is beautiful! May the beauty continue to shine.

  18. Lori Shane 1 month ago

    Your article was so perfect i’ve had the exact feelings and situations many times thank you for a little encouragement

    • Author
      Jessica 1 month ago

      Lori-
      We’re in this together girl. It’s amazing how connecting with others like ourselves can help a person not feel alone and weird. We are just fine.

      • Lori Shane 1 month ago

        Yes we are so nice to have friends

  19. Olivia 1 month ago

    Read your article. I struggle a lot with wondering why I am the way I am. I fight against it daily because I feel like I would lose more than I can gain from dressing. just wanted to say I understand where you are coming from. a lot of people on here do, if not everyone. Thanks.

    • Author
      Jessica 1 month ago

      Caelynn-
      I think when we share our fears we become stronger. We are okay just the way we are.

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